Flotillas

Join us for a week of sailing in paradise, as our late founder Lenny Shabes, set out to teach aspiring sailors to do. To pay tribute to all Lenny has done for the world of sailing, we are calling all sailors to partake in a week of festivities ranging from sundowners to regattas in the […]

Join the Ultimate Sailing Experience! Set sail with us in the stunning British Virgin Islands, whether you want your own boat or prefer to share with others. Certified ASA instructors will be on board, guiding you through ASA 103, 104, and 114 certifications (for an additional fee) as you explore one of the world’s best […]

Sailing the waters around La Paz, Mexico, is a truly magical experience. Nestled in the Sea of Cortez, often referred to as the "Aquarium of the World," La Paz offers crystal-clear turquoise waters, calm seas, and stunning, unspoiled islands just offshore. With no Pacific ground swell, the waters are as smooth as a lake, making […]

Sailing the coastline of Mallorca is a dreamlike journey through the heart of the Mediterranean. As the largest of Spain’s Balearic Islands, Mallorca offers an irresistible blend of rugged coastlines, serene turquoise coves, charming seaside villages, and rich Spanish culture. The island is a sailor’s paradise—calm waters, steady breezes, and countless hidden anchorages create the […]

Set sail on an unforgettable 10-day adventure through the breathtaking waters of Thailand’s southern coast. This flotilla, hosted by Capt. Casey along with seasoned leaders Jean and Mila of Whitecaps Sailing, will take you through emerald lagoons, dramatic limestone karsts, and white-sand beaches in iconic locations like Phang Nga Bay, James Bond Island, Krabi, the […]

Join SailNashville’s BVI Flotilla in December 2025 for eight unforgettable days of sailing, island-hopping, and adventure in paradise. Learn new skills, make new friends, and create lifelong memories on crystal-clear Caribbean waters. Reserve your berth today!

Experience 6 days and 6 nights of unforgettable sailing through the breathtaking British Virgin Islands on our professionally led flotilla—where island-hopping adventure meets laid-back Caribbean charm. Perfect for both seasoned sailors and first-time cruisers, you'll enjoy hands-on sailing by day and relaxed evenings with a fun, supportive group of fellow travelers.

Set your course for a week of Italian magic on the Amalfi Coast Flotilla. This unforgettable journey blends world-class sailing with iconic stops in Capri, Positano, and Procida. Enjoy crystal-clear waters, gourmet cuisine, and sun-soaked coastlines aboard a luxurious catamaran, all with the perfect balance of freedom and expert support. Limited to just three boats, […]

Join fellow boaters in exploring the highlights of the San Juan Islands during the early summer. This flotilla is timed to beat the crowds and enjoy the long hours of daylight during the summer solstice. The San Juan Islands boast sheltered waters, magnificent marine parks, quaint villages and welcoming marinas. Wildlife abounds on the land […]

Experience the magic of a total solar eclipse as it unfolds above the waters of the Mediterranean—an awe-inspiring event witnessed from the deck of a sailing yacht off the coast of Mallorca. This once-in-a-lifetime adventure combines the wonder of the cosmos with the natural beauty, rich history, and coastal charm of one of Spain’s most […]

Join American Sailing and Fairwinds Sailing Greece on a journey from Corfu through the Corfu Islands. Our local captains from Fairwinds Sailing will take us to their favorite anchorages and introduce us to Greece as seen through their eyes. Corfu Island is in the north Ionian Sea, between Italy and Greece (Greek “Ιόνιο Πέλαγος” – […]

Sailing the waters around La Paz, Mexico, is a truly magical experience. Nestled in the Sea of Cortez, often referred to as the "Aquarium of the World," La Paz offers crystal-clear turquoise waters, calm seas, and stunning, unspoiled islands just offshore. With no Pacific ground swell, the waters are as smooth as a lake, making […]

Explore Belize’s paradise islands on your own private luxury catamaran. Learn sailing from ASA certified instructors & crew. Snorkel, kayak, and fish in crystal clear waters. Enjoy gourmet meals & exotic drinks prepared by your crew. Experience a different destination every day on this ultimate sailing vacation!